Holiday optics matter for politicians. These are people who painstakingly spend hours trying to figure out the best setup for a speech or press conference room. They know any move they make will reveal something about themselves. So what does Obama’s vacation -- and those of other leaders -- tell us?

President Barack Obama is reportedly set to head to Martha’s Vineyard, Massachusetts (aka Kennedyland, USA) to force a media connection between him and JFK every time they mention his vacation spot. This is what those of us in the political business call the “halo effect”. JFK is synonymous with Martha’s Vineyard, and it’s likely not a coincidence that he was the last Democratic president anyone liked who’s not still around to present any danger of upstaging Obama. With a job approval rating of 47% and plummeting, the visit will make Obama the only person to be locked in a nosedive in a final approach towards Martha’s Vineyard since JFK Jr’s plane went down.

If his handlers are smart, they’ll keep him in shorts and out of blue jeans. He already had to justify his lack of coolness while throwing like a girl in granny-jeans at a baseball game. And during the campaign last year, he was caught on a hot day in Chicago riding a bike in what looked like the same ones. That’s fine, but voters wanted you to be cool, Barack -- in fact, that was the only reason why some of them voted for you. So maybe try not to let your geek flag fly too much - like the chick who blimps out within a few months of the wedding ring being slid onto her finger.

What kind of vacations did recent Republican presidents take? George W. Bush and Ronald Reagan spent time on their ranches, clearing brush and building things. Ronald Reagan cut down trees and built giant log fences by himself on his ranch in Santa Barbara. When I visited Rancho del Cielo a few years ago, I saw bits of paper on which he had diagrammed out some of the fences he built. He even made the massive table on which the largest tax cut in American history was signed. Was this spin? Perhaps some might say that it was, but if Reagan truly didn’t enjoy building things himself he could have paid someone else to do it and just kicked back by the pool in some cowboy gear for his media close-up. He was an actor by trade, and could have just played the role when the time came. Likewise, I don’t think George W. Bush cleared brush or went pond fishing for the sake of a photo-op before running back inside to paint and file his cuticles.

Russia’s Prime Minister, Vladimir Putin, spent his vacation in the Southern Siberian wilderness riding a horse with his shirt off. This is a case where you really believe this vacation is in total character. No one joins the KGB and works their way up its ranks for show. I think this is truly the kind of person who rises to the level of “big man on campus” in Russia, and we’re seeing him interact with nature and bring it to its knees, much like every Russian woman after viewing his vacation photos. If your country is going to be a socialist or communist one, you’d better give the people the impression that Big Red Daddy has it together. Obama’s granny jeans don’t exactly scream, “Trust me with your money and safety!” Obama was once caught on vacation splashing around in the waves like a “Baywatch” babe. There was no splashing for Putin! Not only was he snapped swimming, but he was sporting rippling arms while performing swimming’s most difficult stroke: the butterfly.

French President Nicolas Sarkozy caught flack for flaking out on a rich pal’s yacht after his 2007 presidential victory. He has since become known as President Bling-Bling, and is currently spending three weeks at the Cap Negre home of his ex-supermodel musician wife, Carla Bruni. They have been snapped looking ridiculously fit while toweling off from a dip. But what a difference a near death experience makes. The vacation comes on the heels of a fainting episode that resulted in a short hospital stay. The guy is obviously killing himself trying to fix France, so at the moment he’s rightfully getting a free pass from his other 64 million countrymen on their multi-week paid vacation. “Mars or Marseille?”, I ask my French friends every summer, knowing the length of vacation would be about the same.

Finally, UK PM Gordon Brown is doing “volunteer work” in his community for his summer break. That’s a safe bet for someone whose gravy train is on the verge of derailing. He could have just stayed put in office and done his “charity work”, because he doesn’t really have any money left to pay his own salary either. People with a poor job outlook in a bad economy usually do best saving up and staying close to home.